Hoechst Celanese Corporation

Charlet R Lindley

Ahmed M Tafesh

George Kvakovszky

Graham N Mott

John R Durrwachter

Arylketoamines are prepared by reacting arylisonitrosoalkanones with hydrogen in the presence of a transition metal catalyst and a liquid carboxylic acid at a temperature of less than about 600.degree. C.

Process for preparing arylketoamines

Arylketoamines are prepared by reacting arylisonitrosoalkanones with hydrogen in the presence of a transition metal catalyst and a liquid carboxylic acid at a temperature of less than about 60.degree. C.

A process for the preparation of .alpha.-chloro-.alpha.-oximino-4-hydroxyacetophenone by reacting nitrosyl chloride with a mixture of 4-hydroxyacetophenone and a strong acid catalyst such as hydrogen chloride is disclosed. The nitrosyl chloride is introduced as a gas into the reactor to contact 4-hydroxyacetophenone and said acid catalyst dissolved in a solvent therein.

Process for preparing

In accordance with the present invention, aromatic ketones are prepared by the acylation of aromatic reactants using boron trifluoride as a catalyst and in a solvent medium comprising anhydrous liquid sulfur dioxide. The acylation proceeds in accordance with the equation I: ##STR1## wherein n ranges from 5 to 9, Ar is phenylene and n is 5, naphthalene and n is 7, or a bis phenylene radical having the structure: ##STR2## and n is 9; wherein Z is selected from the group consisting of a covalent carbon to carbon bond, O, S, SO.sub.2, C.dbd.O and C.sub.1 to C.sub.3 alkylene or alkylidene, X is selected from the group consisting of H, OH, halogen, C.sub.1 to C.sub.6 alkyl C.sub.1 to C.sub.6 alkoxy and combinations thereof, R is an alkyl group containing from 1 to about 16 carbon atoms and Y is selected from the group consisting of hydroxy, acyloxy and halogen. The acylation process of this invention gives rise to aromatic ketones which are highly selectively acylated at the activated ring carbon and also yields a high ratio of conversion of the aromatic starting material. The process also provides a faster rate of reaction than analogous processes and affords the opportunity to recover large quantities of the BF.sub.3 catalyst as well as the SO.sub.2 solvent for recycle, thus offering improved economy and efficiencies.

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Portland, TX, United States of America

Charlet R Lindley